Oxycholesterol - Misplaced Pages

Oxycholesterol
Names

IUPAC name 5,6β-Epoxy-5β-cholestan-3β-ol
Systematic IUPAC name (3S,4aS,5aR,6aS,6bS,9R,9aR,11aS,11bR)-9a,11b-Dimethyl-9-hexadecahydrocyclopentaphenanthrooxiren-3-ol
Identifiers
CAS Number	4025-59-6
3D model (JSmol)	Interactive image
ChemSpider	97204
PubChem CID	108109
UNII	PFD65A4X36
CompTox Dashboard (EPA)	DTXSID501314152
InChI InChI=1S/C27H46O2/c1-17(2)7-6-8-18(3)21-9-10-22-20-15-24-27(29-24)16-19(28)11-14-26(27,5)23(20)12-13-25(21,22)4/h17-24,28H,6-16H2,1-5H3/t18-,19+,20+,21-,22+,23+,24-,25-,26-,27-/m1/s1Key: PRYIJAGAEJZDBO-DTLXENBRSA-N InChI=1/C27H46O2/c1-17(2)7-6-8-18(3)21-9-10-22-20-15-24-27(29-24)16-19(28)11-14-26(27,5)23(20)12-13-25(21,22)4/h17-24,28H,6-16H2,1-5H3/t18-,19+,20+,21-,22+,23+,24-,25-,26-,27-/m1/s1Key: PRYIJAGAEJZDBO-DTLXENBRBQ
SMILES C(CCCC(C)C)1CC21(CC32C45(3(CC(C5)O)C)O4)C
Properties
Chemical formula	C₂₇H₄₆O₂
Molar mass	402.663 g·mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). Infobox references

Chemical compound

Oxycholesterol or 5,6-epoxycholesterol is a form of oxidized cholesterol implicated in atherosclerosis. It is commonly formed from the reaction of fats and oxygen during high temperature cooking such as frying.

In a study about the effects of oxycholesterol in rabbits with induced hypercholesterolemia, it was shown that compared feeding rabbits cholesterol and unoxidized cholesterol, feeding rabbits oxycholesterol resulted in their developing much higher levels of total cholesterol and low-density lipoprotein cholesterol. It is also shown to increase the amount of homocysteine and asymmetric dimethylarginine levels in the rabbits. An abundance of homocysteine leads to an organism with greater chances of endothelial cell injury which can then lead to coronary artery disease. Asymmetric dimethylarginine is shown to cause adverse effects on humans in the form of cardiovascular and metabolic diseases. Therefore it was concluded that adding oxycholesterol into diets of animals with hypercholesterolemia increases endothelial dysfunction and inflammatory response.

References

"Little known type of cholesterol may pose the greatest heart disease risk". August 20, 2009.
Wielkoszyński, Tomasz; Zalejska-Fiolka, Jolanta; Strzelczyk, Joanna K.; Owczarek, Aleksander J.; Cholewka, Armand; Furmański, Marcin; Stanek, Agata (2018). "Oxysterols Increase Inflammation, Lipid Marker Levels and Reflect Accelerated Endothelial Dysfunction in Experimental Animals". Mediators of Inflammation. 2018: 2784701. doi:10.1155/2018/2784701. ISSN 0962-9351. PMC 5866902. PMID 29713239.

Cardiovascular disease (vessels)

Arteries, arterioles
and capillaries

Inflammation	Arteritis Aortitis Buerger's disease
Arteriosclerosis	Atherosclerosis Foam cell Fatty streak Atheroma Cholesterol LDL Oxycholesterol Trans fat Monckeberg's arteriosclerosis Hyaline arteriolosclerosis Hyperplastic arteriolosclerosis
Peripheral artery disease	Stenosis Carotid artery stenosis Renal artery stenosis Aortoiliac occlusive disease Critical limb ischemia Degos disease Erythromelalgia Fibromuscular dysplasia Hepatic artery thrombosis Intermittent claudication Raynaud's phenomenon
Aneurysm / dissection / pseudoaneurysm	torso: Aortic aneurysm Abdominal aortic aneurysm Thoracic aortic aneurysm Aneurysm of sinus of Valsalva Aortic dissection Aortic rupture Coronary artery aneurysm head / neck Intracranial aneurysm Intracranial berry aneurysm Carotid artery dissection Vertebral artery dissection Familial aortic dissection
Vascular malformation	Arteriovenous fistula Arteriovenous malformation Telangiectasia Hereditary hemorrhagic telangiectasia Generalized essential telangiectasia
Vascular nevus	Cherry hemangioma Halo nevus Spider angioma

Veins

Inflammation	Phlebitis
Venous thrombosis / Thrombophlebitis	primarily lower limb Deep vein thrombosis abdomen Hepatic veno-occlusive disease Budd–Chiari syndrome May–Thurner syndrome Portal vein thrombosis Renal vein thrombosis upper limb / torso Mondor's disease Paget–Schroetter disease Pulmonary embolism head Cerebral venous sinus thrombosis Post-thrombotic syndrome
Varicose veins	Gastric varices Portacaval anastomosis Caput medusae Esophageal varices Hemorrhoid Varicocele
Other	Chronic venous insufficiency Chronic cerebrospinal venous insufficiency Superior vena cava syndrome Inferior vena cava syndrome Venous ulcer

Arteries or veins

Blood pressure

Hypertension	Hypertensive heart disease Hypertensive emergency Hypertensive nephropathy Essential hypertension Secondary hypertension Renovascular hypertension Benign hypertension Pulmonary hypertension Systolic hypertension White coat hypertension
Hypotension	Orthostatic hypotension Shock (circulatory)

Categories:

See also

References